Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:06:01 UTC |
---|
Update date | 2020-09-17 15:38:22 UTC |
---|
Primary ID | FDB003949 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Hypoxanthine |
---|
Description | Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Hypoxanthine is a moderately basic compound (based on its pKa). Hypoxanthine exists in all living species, ranging from bacteria to humans. Within humans, hypoxanthine participates in a number of enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, hypoxanthine and phosphoribosyl pyrophosphate can be biosynthesized from inosinic acid; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, hypoxanthine is involved in purine metabolism. Outside of the human body, Hypoxanthine is found, on average, in the highest concentration within beers and milk (cow). Hypoxanthine has also been detected, but not quantified in, several different foods, such as pigeon pea, green vegetables, lovages, gram beans, and arrowhead. This could make hypoxanthine a potential biomarker for the consumption of these foods. Hypoxanthine is a potentially toxic compound. |
---|
CAS Number | 68-94-0 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
6(1H)-Purinone | ChEBI | 6-Oxopurine | ChEBI | 9H-Purin-6(1H)-one | ChEBI | Hyp | ChEBI | Purin-6(1H)-one | ChEBI | Purine-6-ol | ChEBI | 1,7-Dihydro-6H-purin-6-one | HMDB | 1,7-Dihydro-6H-purine-6-one | HMDB | 1H,7H-Hypoxanthine | HMDB | 3H-Purin-6-ol | HMDB | 4-Hydroxy-1H-purine | HMDB | 6-Hydroxy-1H-purine | HMDB | 6-Hydroxypurine | HMDB | 7H-Purin-6-ol | HMDB | 9H-Purin-6-ol | HMDB | Hypoxanthine enol | HMDB | Purin-6(3H)-one | HMDB | Purin-6-ol | HMDB | Sarcine | HMDB | Sarkin | HMDB | Sarkine | HMDB | 1,7-dihydro-6H-Purin-6-one | HMDB | 1,9-Dihydro-purin-6-one | biospider | 6H-Purin-6-one, 1,7-dihydro- | biospider | 6H-Purin-6-one, 1,9-dihydro- | biospider | Hypoxanthine | biospider | Imidazo[5,4-d]pyrimidine, 6-hydroxy- | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C5H4N4O |
---|
IUPAC name | 7H-purin-6-ol |
---|
InChI Identifier | InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) |
---|
InChI Key | FDGQSTZJBFJUBT-UHFFFAOYSA-N |
---|
Isomeric SMILES | OC1=NC=NC2=C1NC=N2 |
---|
Average Molecular Weight | 136.1115 |
---|
Monoisotopic Molecular Weight | 136.03851077 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Imidazopyrimidines |
---|
Sub Class | Purines and purine derivatives |
---|
Direct Parent | Hypoxanthines |
---|
Alternative Parents | |
---|
Substituents | - 6-oxopurine
- Hypoxanthine
- Pyrimidone
- Pyrimidine
- Azole
- Imidazole
- Vinylogous amide
- Heteroaromatic compound
- Azacycle
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Needles | CCD |
---|
Mass Composition | C 44.12%; H 2.96%; N 41.16%; O 11.75% | CCD |
---|
Melting Point | Mp 360° | CCD |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | 0.7 mg/mL at 23 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | -1.11 | HANSCH,C ET AL. (1995) |
---|
Experimental pKa | p Ka11.91 ( 20° ) p Ka28.96 ( 20° ) p Ka312.18 ( 20° ) | CCD |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-000i-8900000000-ebf57ea530a2d4e31ffa | Spectrum | GC-MS | Hypoxanthine, 2 TMS, GC-MS Spectrum | splash10-0159-3970000000-0d844fae4a1ffe158823 | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-014i-1790000000-ae93bf8bf07b30b65e1a | Spectrum | GC-MS | Hypoxanthine, 2 TMS, GC-MS Spectrum | splash10-00di-9340000000-1184c503fb61344c4853 | Spectrum | GC-MS | Hypoxanthine, 2 TMS, GC-MS Spectrum | splash10-014i-3590000000-a419976950afe7934cbc | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-000i-9800000000-9c266d6963658e9d2cf1 | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-0159-3970000000-0d844fae4a1ffe158823 | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-014i-1790000000-ae93bf8bf07b30b65e1a | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-00di-9340000000-1184c503fb61344c4853 | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-014i-3590000000-a419976950afe7934cbc | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-014i-2890000000-3be4d08be45781881bc1 | Spectrum | GC-MS | Hypoxanthine, non-derivatized, GC-MS Spectrum | splash10-014i-1590000000-bb6f003bfa7bd04628a1 | Spectrum | Predicted GC-MS | Hypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a5i-8900000000-e20eb5d939a2c406a6e2 | Spectrum | Predicted GC-MS | Hypoxanthine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0613-5900000000-be0624b928ba71cc797d | Spectrum | Predicted GC-MS | Hypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hypoxanthine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hypoxanthine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hypoxanthine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0930030000-56ea204dcb077bc174c2 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-9000000000-4c2d1980f9e5e4b720a5 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-000i-0900000000-26b3c93bc9dea5a88032 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-1900000000-c367cd4c23aea0f74ecb | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000l-8900000000-91e35cdcc11d357119f0 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0006-9100000000-4fb8f4ee2d35aa874617 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-014l-9000000000-7934b3037f39d69fc40a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-014i-9000000000-ad93e267446292bf247b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-1900000000-c367cd4c23aea0f74ecb | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000l-8900000000-f8c3fcf312f201115f52 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9100000000-1088187ef16c41e5fd58 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014l-9000000000-7934b3037f39d69fc40a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-9000000000-ad93e267446292bf247b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-9000000000-fba535f8767b852493f1 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-000i-0900000000-26b3c93bc9dea5a88032 | Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-000l-5900000000-835823cc21e116df8128 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9000000000-6eabf590960d6c5dd018 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00kf-9000000000-a16f6a9310d83b058967 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9100000000-0ddabb4a93af99de1aa6 | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-014l-9000000000-54ceed9029123cd72f47 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-b85ebc5bb10dca9de18e | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0gi0-0900000000-97b1e5c9521910e9085a | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00kr-0900000000-b3eb906d6973911451f6 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000l-5900000000-6acc72db72a1b37b957c | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000l-8900000000-9c590766cbef043e3eff | Spectrum |
|
---|
NMR | |
---|
External Links |
---|
ChemSpider ID | 768 |
---|
ChEMBL ID | CHEMBL1427 |
---|
KEGG Compound ID | C00262 |
---|
Pubchem Compound ID | 790 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 17368 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB04076 |
---|
HMDB ID | HMDB00157 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | BVX59-I:BVX59-I |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | HYPOXANTHINE|HYPOXANTHIN |
---|
BIGG ID | 34434 |
---|
KNApSAcK ID | Not Available |
---|
HET ID | HPA |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Hypoxanthine |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Purine nucleoside phosphorylase | PNP | P00491 | Equilibrative nucleoside transporter 2 | SLC29A2 | Q14542 |
|
---|
Pathways | |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|